Chapter 4
Carbon and the Molecular
Diversity of Life
Overview: Carbon: The Backbone of Life
• Living organisms consist mostly of carbon-based
compounds
• Carbon is unparalleled in its ability to form large,
complex, and diverse molecules
• Proteins, DNA, carbohydrates, and other
molecules that distinguish living matter are all
composed of carbon compounds
Organic chemistry is the study of carbon
compounds
• Organic chemistry is the study of compounds
that contain carbon
• Organic compounds range from simple
molecules to colossal ones
• Most organic compounds contain hydrogen
atoms in addition to carbon atoms
• Vitalism, the idea that organic compounds
arise only in organisms, was disproved when
chemists synthesized these compounds
• Mechanism is the view that all natural
phenomena are governed by physical and
chemical laws
Organic Molecules and the Origin of Life
on Earth
• Stanley Miller’s classic experiment
demonstrated the abiotic synthesis of
organic compounds
• Experiments support the idea that abiotic
synthesis of organic compounds, perhaps
near volcanoes, could have been a stage in
the origin of life
The Formation of Bonds with Carbon
• With four valence electrons, carbon can form
four covalent bonds with a variety of atoms
• This ability makes large, complex molecules
possible
• In molecules with multiple carbons, each carbon
bonded to four other atoms has a tetrahedral
shape
• However, when two carbon atoms are joined by
a double bond, the atoms joined to the carbons
are in the same plane as the carbons
Figure 4.3
Name and
Comment
Molecular
Formula
(a) Methane
CH4
(b) Ethane
C2H6
(c) Ethene
(ethylene)
C2H4
Structural
Formula
Ball-andStick Model
Space-Filling
Model
Figure 4.4
Hydrogen
(valence  1)
Oxygen
(valence  2)
Nitrogen
(valence  3)
Carbon
(valence  4)
• Carbon atoms can partner with atoms other than
hydrogen; for example:
– Carbon dioxide: CO2
– Urea: CO(NH2)2
Molecular Diversity Arising from Carbon
Skeleton Variation
• Carbon chains form the skeletons of most
organic molecules
• Carbon chains vary in length and shape
Figure 4.5
(c) Double bond position
(a) Length
Ethane
Propane
(b) Branching
Butane
1-Butene
2-Butene
(d) Presence of rings
2-Methylpropane
(isobutane)
Cyclohexane
Benzene
Hydrocarbons
• Hydrocarbons are organic molecules
consisting of only carbon and hydrogen
• Many organic molecules, such as fats, have
hydrocarbon components
• Hydrocarbons can undergo reactions that
release a large amount of energy
Isomers
• Isomers are compounds with the same
molecular formula but different structures and
properties
– Structural isomers have different covalent
arrangements of their atoms
– Cis-trans isomers have the same covalent
bonds but differ in spatial arrangements
– Enantiomers are isomers that are mirror
images of each other
Figure 4.7
(a) Structural isomers
(b) Cis-trans isomers
cis isomer: The two Xs
are on the same side.
trans isomer: The two Xs
are on opposite sides.
(c) Enantiomers
CO2H
CO2H
H
NH2
CH3
L isomer
NH2
H
CH3
D isomer
• Enantiomers are important in the
pharmaceutical industry
• Two enantiomers of a drug may have different
effects
• Usually only one isomer is biologically active
• Differing effects of enantiomers demonstrate
that organisms are sensitive to even subtle
variations in molecules
Figure 4.8
Drug
Condition
Ibuprofen
Pain;
inflammation
Albuterol
Effective
Enantiomer
Ineffective
Enantiomer
S-Ibuprofen
R-Ibuprofen
R-Albuterol
S-Albuterol
Asthma
A few chemical groups are key to the
functioning of biological molecules
• Distinctive properties of organic molecules depend
on the carbon skeleton and on the molecular
components attached to it
• A number of characteristic groups can replace the
hydrogens attached to skeletons of organic
molecules
• Functional groups are the components of organic
molecules that are most commonly involved in
chemical reactions
• The number and arrangement of functional groups
give each molecule its unique properties
Figure 4.UN02
Estradiol
Testosterone
• The seven functional groups that are most
important in the chemistry of life:
–
–
–
–
–
–
–
Hydroxyl group
Carbonyl group
Carboxyl group
Amino group
Sulfhydryl group
Phosphate group
Methyl group
Figure 4.9a
Hydroxyl
STRUCTURE
(may be written
HO—)
EXAMPLE
Ethanol
Alcohols
(Their specific
names usually
end in -ol.)
NAME OF
COMPOUND
• Is polar as a result
of the electrons
spending more
time near the
electronegative
oxygen atom.
FUNCTIONAL
PROPERTIES
• Can form hydrogen
bonds with water
molecules, helping
dissolve organic
compounds such
as sugars.
Figure 4.9b
Carbonyl
STRUCTURE
Ketones if the carbonyl
group is within a
carbon skeleton
NAME OF
COMPOUND
Aldehydes if the carbonyl
group is at the end of the
carbon skeleton
EXAMPLE
Acetone
Propanal
• A ketone and an
aldehyde may be
structural isomers
with different properties,
as is the case for
acetone and propanal.
• Ketone and aldehyde
groups are also found
in sugars, giving rise
to two major groups
of sugars: ketoses
(containing ketone
groups) and aldoses
(containing aldehyde
groups).
FUNCTIONAL
PROPERTIES
Figure 4.9c
Carboxyl
STRUCTURE
Carboxylic acids, or organic
acids
NAME OF
COMPOUND
EXAMPLE
• Acts as an acid; can
FUNCTIONAL
PROPERTIES
donate an H+ because the
covalent bond between
oxygen and hydrogen is so
polar:
Acetic acid
Nonionized
Ionized
• Found in cells in the ionized
form with a charge of 1– and
called a carboxylate ion.
Figure 4.9d
Amino
STRUCTURE
Amines
NAME OF
COMPOUND
EXAMPLE
•
FUNCTIONAL
PROPERTIES
Acts as a base; can
pick up an H+ from the
surrounding solution
(water, in living
organisms):
Glycine
Nonionized
•
Ionized
Found in cells in the
ionized form with a
charge of 1.
Figure 4.9e
Sulfhydryl
STRUCTURE
Thiols
NAME OF
COMPOUND
•
Two sulfhydryl groups can
react, forming a covalent
bond. This “cross-linking”
helps stabilize protein
structure.
FUNCTIONAL
PROPERTIES
•
Cross-linking of cysteines
in hair proteins maintains
the curliness or straightness
of hair. Straight hair can be
“permanently” curled by
shaping it around curlers
and then breaking and
re-forming the cross-linking
bonds.
(may be
written HS—)
EXAMPLE
Cysteine
Figure 4.9f
Phosphate
STRUCTURE
Organic phosphates
EXAMPLE
•
FUNCTIONAL
Contributes negative
charge to the molecule PROPERTIES
of which it is a part
(2– when at the end of
a molecule, as at left;
1– when located
internally in a chain of
phosphates).
•
Molecules containing
phosphate groups have
the potential to react
with water, releasing
energy.
Glycerol phosphate
NAME OF
COMPOUND
Figure 4.9g
Methyl
STRUCTURE
Methylated compounds
EXAMPLE
•
Addition of a methyl group FUNCTIONAL
PROPERTIES
to DNA, or to molecules
bound to DNA, affects the
expression of genes.
•
Arrangement of methyl
groups in male and female
sex hormones affects their
shape and function.
5-Methyl cytidine
NAME OF
COMPOUND
ATP: An Important Source of Energy for
Cellular Processes
• One phosphate molecule, adenosine
triphosphate (ATP), is the primary energytransferring molecule in the cell
• ATP consists of an organic molecule called
adenosine attached to a string of three
phosphate groups
Figure 4. UN04
Adenosine
The Chemical Elements of Life: A Review
• The versatility of carbon makes possible the
great diversity of organic molecules
• Variation at the molecular level lies at the
foundation of all biological diversity
Figure 4. UN05
Reacts
with H2O
Adenosine
Adenosine
ATP
Inorganic
phosphate
ADP
Energy